Ashley Mayhew Dineen
Awards
Press
Specialties
Areas Covered
​ Darien
Charity
Community Fund Darien - Unsung Hero Award 2020
Meet a Mom: Meet Ashley Dineen of Tiny Miracles
★★★★★
"Ashley’s knowledge of the area is encyclopedic, her attention to detail without equal...but what makes her the best agent we’ve ever dealt with is her thorough, thoughtful handling of the entire process: from identifying the right area for us to narrowing down our list of houses, and then from negotiating to closing and beyond. Ashley was with us every step of the way, and as a consequence of that, we feel even better about the house we bought. (Can’t really think of a better recommendation than that.)"
★★★★★
"Ashley was raised in Darien so she is the town expert. This is especially helpful because she can put you in touch with a mortgage broker, attorney the closing, etc. She will help you find the best home you based on your criteria. Coming from Manhattan and apartment living 20+ years, we had some very specific needs our family and she was able to show us homes in our price range that fit those requests. She is a pleasure to work with and she is very tied into the community."
Ashley Dineen is a leading real estate advisor in Darien and across Fairfield County, known for her discretion, market expertise, and unwavering integrity. A lifelong Darien resident, Ashley brings an authentic understanding of the community and a thoughtful, strategic approach to every client relationship.
In 2025, Ashley and her team were recognized as the #1 team in Darien for sales volume, operating from Compass Darien, the #1 office in the market. Her success is rooted in precision, preparation, and trust—values that guide every transaction. Integrity is the foundation of Ashley’s practice, guiding her commitment to transparency, thoughtful counsel, and unwavering advocacy for her clients’ best interests.
Ashley has earned national recognition for her work, including being named to The Wall Street Journal’s America’s Best Real Estate Professionals for four consecutive years. She is also a member of REALM, an invitation-only network representing the top 1% of real estate advisors worldwide, offering clients unparalleled reach and access.
Known for her ability to articulate a property’s true value and align clients with homes that reflect their lifestyle and long-term goals, Ashley delivers a highly personalized, elevated experience—whether representing a significant estate or a primary residence.
Beyond real estate, Ashley serves as President of the Board of Directors for The Tiny Miracles Foundation, supporting families with premature infants in Fairfield and New Haven Counties, a mission shaped by her own family’s experience.
Ashley lives in Darien with her husband Duke and their three college-aged daughters. Her reputation—built on integrity, discretion, and results—has made her a trusted advisor to discerning buyers and sellers who expect excellence at every level.
Ashley Mayhew Dineen’s Listings
$15,000,000
- 5
- Bedrooms
- 10
- Bathrooms
- 10,197
- Square Feet
- 9.26
- Acres